5 Must-See Summer Festivals

Mark Your Calendar: Another 5 Bucket-List Fests

As promised, we’ve brought you festivals worthy of any bucket list in winter, spring, and now summer. The third in this series of articles offers the opportunity for insight in Upstate New York, flights of fancy in Chicago, and wine flights in California. Along the way, there are stops in the Old West, where the cowboys (and cowgirls) ride well—whether by horseback or by Harley. Regardless, the events in this list will take you clear across the country and clear though the summer.

#1: Lily Dale Assembly, Lily Dale, NY

In the 1870s, a group of Spiritualists, among them mediums and healers, established a summer campground at Lake Cassadaga in southwestern New York. Eventually, many settled here permanently. The gated Victorian hamlet, part of the town of Pomfret, is now home to a couple hundred people “devoted to the service of God, Spirit, and Mankind.” Year-round, there are dozens of registered mediums with whom you can schedule readings. But that number and the overall population swell considerably during the June to September Lily Dale Assembly season, now in its 135th year. Inns are booked to capacity, and cafes and shops fill with visitors who have come for readings, services, and workshops. On arrival, stop by the town museum, housed in a former one-room schoolhouse, to learn more about the community’s beliefs as well as its history. June 27–August 31, 2014.

#2: Cheyenne Frontier Days, Cheyenne, WY

When you’ve been around for more than a century, similar festivals start calling you the granddaddy of them all. More cowboys register to compete in the nine rodeos of Cheyenne Frontier Days han any other PRCA event, and A-list country and rock stars like Brad Paisley, Lady Antebellum, John Mellancamp, and Kid Rock come to perform. So legendary is Frontier Days that each year a silversmith designs a new commemorative belt buckle. Don’t miss the roping, wrestling, and riding events—along with those nightly concerts. Four times throughout the festival a parade of floats, marching bands, antique carriages, and riders in period dress fills the streets of historic downtown. You can also explore the Indian Village, which features Native American dancing and handicrafts, or Frontier Town, where you can learn what life was like for early Western settlers. There’s also a carnival midway and the chance to sample real ranch cooking from chuck wagons. July 18–27, 2014.

#3: Sturgis Motorcycle Rally, Sturgis, SD

For a week each August, the Black Hills of South Dakota rumble with the full-throttled roar of motorcycles. This small town has become one of the world’s most famous destinations thanks to the Sturgis Motorcycle Rally, which it has hosted since 1938. It draws a half-million people—almost doubling the state’s population—and spills over into all the surrounding towns with events that include races, concerts, parties, and scenic tours. The epicenter, though, is downtown Sturgis, where the bikes line the streets, and the partying goes on all night. Don’t miss the Sturgis Motorcycle Museum & Hall of Fame. And if you’ve ever been tempted to get a tattoo, this might be the week and place to do it—if you can tear yourself away from the concerts, roller derby, motorcycle stunt shows, and other events. August 4–10, 2014.

#4: Chicago Air and Water Show, Chicago, IL

This dazzling display of air power and aquatic prowess has drawn scores of spectators to the city’s lakefront each August since 1959. With 2 million attendees, the Chicago Air and Water Show is the world’s largest aviation event—and it is loud. It’s also free. In the air, pilots and parachute teams amaze the crowd with their feats of derring-do. On Lake Michigan, water-skiing and boat-jumping performers are equally fearless. Though the hub is North Avenue Beach, there are excellent viewpoints all along the 28-mile lakefront. And, with the city’s storied skyline behind you, it’s hard to imagine a more scenic urban setting. Checklist: Sunscreen, sunglasses, ear plugs, bottled water, and binoculars. Tip: Take public transportation or park at Millennium Park Garage and hop the free shuttle to (and from) North Avenue Beach. August 16–17, 2014.

#5: Sonoma Wine Country Weekend, Sonoma, CA

The grape-to-glass Sonoma Wine Country Weekend bills itself as California Wine Country’s premier wine and food festival. Every year, more than 200 wineries and chefs give participants all types of distinctive epicurean experiences. At estates across the county, you can take a seat at chic lunches and dinners, where winemakers pair pours with innovative cuisine. Some meals seat as few as six guests, offering a rare chance to chat with vintners in an intimate setting. The grand event, Taste of Sonoma County, grants you access to entertaining wine seminars, lively cooking demos, tastings, shopping expeditions, and get-your-boots-dirty vineyard tours. August 29–31, 2014.